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4-O-p-coumaroylqunic acid

Family: Plantae - Lamiaceae
Kingdom: Plantae
Class: Phenolic

Canonical Smiles	O=C(OC1[C@H](O)CC(C[C@H]1O)(O)C(=O)O)/C=C/c1ccc(cc1)O
InChI	InChI=1S/C16H18O8/c17-10-4-1-9(2-5-10)3-6-13(20)24-14-11(18)7-16(23,15(21)22)8-12(14)19/h1-6,11-12,14,17-19,23H,7-8H2,(H,21,22)/b6-3+/t11-,12-,14?,16?/m1/s1
InChIKey	XWRHBGVVCOSNKO-OPGYGNEESA-N
Formula	C₁₆H₁₈O₈
HBA	7
HBD	5
MW	338.31
Rotatable Bonds	4
TPSA	144.52
LogP	-0.35
Number Rings	2
Number Aromatic Rings	1
Heavy Atom Count	24
Formal Charge	0
Fraction CSP3	0.38
Exact Mass	338.1
Number of Lipinski Rule Violations	0

#	Species	Family	Kingdom	NCBI Taxonomy ID
1	Rosmarinuseriocalyx	Lamiaceae	Plantae	—

Showing of synonyms

Boudiar T, Lozano-Sánchez J, et al. (2019). Phytochemical characterization of bioactive compounds composition of Rosmarinus eriocalyx by RP–HPLC–ESI–QTOF–MS. Natural product research, 2019, 33(15), 2208-2214. [View] [PubMed]

Pubchem: 5281766

Cas: 1108200-72-1

Gnps: CCMSLIB00000854975

Zinc: ZINC000004098727

Nmrshiftdb2: 60029634

No compound-protein relationship available.

SMILES: C1CCCCC1OC(=O)C=Cc2ccccc2

Level: 1

Mol. Weight: 338.31 g/mol

SMILES: C1CCCCC1

Level: 0

Mol. Weight: 338.31 g/mol

SMILES: c1ccccc1

Level: 0

Mol. Weight: 338.31 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp): -6.12
Human Oral Bioavailability 20%: Non-Bioavailable
Human Intestinal Absorption: Absorbed
Madin-Darby Canine Kidney: -3.65
Human Oral Bioavailability 50%: Non-Bioavailable
P-Glycoprotein Inhibitor: Non-Inhibitor
P-Glycoprotein Substrate: Non-Substrate
Skin Permeability: -3.63

Distribution

Blood-Brain Barrier (CNS): -
Blood-Brain Barrier: Non-Penetrable
Fraction Unbound (Human): 0.68
Plasma Protein Binding: 45.54
Steady State Volume of Distribution: -

Metabolism

Breast Cancer Resistance Protein: Non-Inhibitor
CYP 1A2 Inhibitor: Non-Inhibitor
CYP 1A2 Substrate: Non-Substrate
CYP 2C19 Inhibitor: Non-Inhibitor
CYP 2C19 Substrate: Non-Substrate
CYP 2C9 Inhibitor: Non-Inhibitor
CYP 2C9 Substrate: Non-Substrate
CYP 2D6 Inhibitor: Non-Inhibitor
CYP 2D6 Substrate: Non-Substrate
CYP 3A4 Inhibitor: Non-Inhibitor
CYP 3A4 Substrate: Non-Substrate
OATP1B1: Non-Inhibitor
OATP1B3: Non-Inhibitor

Excretion

Clearance: 4.9
Organic Cation Transporter 2: Non-Inhibitor
Half-Life of Drug: -

Toxicity

AMES Mutagenesis: Safe
Avian: Safe
Bee: Safe
Bioconcentration Factor: -1.26
Biodegradation: Toxic
Carcinogenesis: Safe
Crustacean: Safe
Liver Injury I (DILI): Safe
Eye Corrosion: Safe
Eye Irritation: Safe
Maximum Tolerated Dose: 0.4
Liver Injury II: Toxic
hERG Blockers: Safe
Daphnia Maga: 3.9
Micronucleos: Toxic
NR-AhR: Safe
NR-AR: Safe
NR-AR-LBD: Safe
NR-Aromatase: Safe
NR-ER: Safe
NR-ER-LBD: Safe
NR-GR: Safe
NR-PPAR-gamma: Safe
NR-TR: Safe
T. Pyriformis: 1.05
Rat (Acute): 2.04
Rat (Chronic Oral): 3.04
Fathead Minnow: 3.8
Respiratory Disease: Safe
Skin Sensitisation: Toxic
SR-ARE: Safe
SR-ATAD5: Safe
SR-HSE: Safe
SR-MMP: Safe
SR-p53: Safe

General Properties

Boiling Point: 391.25
Hydration Free Energy: -9.59
Log(D) at pH=7.4: -1.7
Log(P): 0.01
Log S: -1.7
Log(Vapor Pressure): -12.34
Melting Point: 204.49
pKa Acid: 2.68
pKa Basic: 6.89

Protein Name	UniProt ID	Entry Name	Species	#Pharmacophore Points	Probability (0.7 ≤ Tversky Score ≤ 1.0)
Dihydrofolate reductase	P00378	DYR_CHICK	Gallus gallus	3	0.8971
ABC-type polar amino acid transport system, ATPase component	Q8RCC2	Q8RCC2_CALS4	Caldanaerobacter subterraneus subsp. tengcongensis	3	0.8573
Pantothenate synthetase	P9WIL5	PANC_MYCTU	Mycobacterium tuberculosis	3	0.8150
Thymidylate synthase	P0A884	TYSY_ECOLI	Escherichia coli	2	0.8096
Endoplasmin	P41148	ENPL_CANLF	Canis lupus familiaris	3	0.7875
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7858
Polyribonucleotide nucleotidyltransferase	A7ZS61	PNP_ECO24	Escherichia coli O139:H28	3	0.7789
Squalene synthase	P37268	FDFT_HUMAN	Homo sapiens	4	0.7748
Nicotinate-nucleotide--dimethylbenzimidazole phosphoribosyltransferase	Q05603	COBT_SALTY	Salmonella typhimurium	2	0.7511
Formate--tetrahydrofolate ligase	P21164	FTHS_MOOTH	Moorella thermoacetica	3	0.7481
Aldos-2-ulose dehydratase	P84193	AUD_PHACH	Phanerodontia chrysosporium	3	0.7462
LIM domain kinase 1	P53667	LIMK1_HUMAN	Homo sapiens	2	0.7437
Genome polyprotein	A0EKU1	A0EKU1_9FLAV	Meaban virus	3	0.7416
3-hydroxyanthranilate 3,4-dioxygenase	Q1LCS4	3HAO_CUPMC	Cupriavidus metallidurans	2	0.7400
Glycogen synthase kinase-3 beta	P49841	GSK3B_HUMAN	Homo sapiens	2	0.7371
UTP-monosaccharide-1-phosphate uridylyltransferase	D3G6S4	D3G6S4_LEIMA	Leishmania major	3	0.7333
Heat shock protein HSP 90-alpha	P07900	HS90A_HUMAN	Homo sapiens	2	0.7305
Serine/threonine-protein kinase SKY1	Q03656	SKY1_YEAST	Saccharomyces cerevisiae	2	0.7286
Photosynthetic reaction center cytochrome c subunit	P07173	CYCR_BLAVI	Blastochloris viridis	2	0.7281
Ephrin type-B receptor 2	P54763	EPHB2_MOUSE	Mus musculus	2	0.7258
2-aminohexano-6-lactam racemase	Q7M181	ACLR_ACHOB	Achromobacter obae	2	0.7244
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7213
Capsid protein	Q9WBP8	Q9WBP8_9VIRU	Adeno-associated virus - 1	2	0.7207
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7205
Ephrin type-A receptor 2	P29317	EPHA2_HUMAN	Homo sapiens	3	0.7196
Hygromycin-B 4-O-kinase	P00557	KHYB_ECOLX	Escherichia coli	3	0.7191
Tetracycline repressor protein class D	P0ACT4	TETR4_ECOLX	Escherichia coli	3	0.7191
Eukaryotic translation initiation factor 4E type 3	Q9DBB5	IF4E3_MOUSE	Mus musculus	3	0.7172
Albumin	P02768	ALBU_HUMAN	Homo sapiens	2	0.7161
Adenosine 5'-monophosphoramidase HINT1	P80912	HINT1_RABIT	Oryctolagus cuniculus	3	0.7157
Pancreatic alpha-amylase	P04746	AMYP_HUMAN	Homo sapiens	2	0.7152
Mitogen-activated protein kinase 1	P28482	MK01_HUMAN	Homo sapiens	3	0.7133
Myosin heavy chain kinase A	P42527	MHCKA_DICDI	Dictyostelium discoideum	2	0.7130
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase	Q81LL4	MTNN_BACAN	Bacillus anthracis	2	0.7119
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7092
Probable bifunctional SAT/APS kinase	O67174	SATC_AQUAE	Aquifex aeolicus	3	0.7090
Serine/threonine-protein kinase Chk2	O96017	CHK2_HUMAN	Homo sapiens	2	0.7089
DNA gyrase subunit A	P0AES5	GYRA_SHIFL	Shigella flexneri	3	0.7074
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7072
Fructose-1,6-bisphosphatase 1	P09467	F16P1_HUMAN	Homo sapiens	2	0.7055
Acetolactate synthase, chloroplastic	P17597	ILVB_ARATH	Arabidopsis thaliana	2	0.7052
Kinesin-like protein KIF11	P52732	KIF11_HUMAN	Homo sapiens	3	0.7051
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7048
Purine nucleoside phosphorylase DeoD-type	B1JL34	DEOD_YERPY	Yersinia pseudotuberculosis serotype O:3	2	0.7045
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7045
Biotin carboxylase	P24182	ACCC_ECOLI	Escherichia coli	2	0.7039
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7035
Anthranilate phosphoribosyltransferase	P00500	TRPD_ACIAD	Acinetobacter baylyi	2	0.7035
Capsid protein VP1	O56137	O56137_9VIRU	Adeno-associated virus - 6	3	0.7021
Chalcone synthase 2	P30074	CHS2_MEDSA	Medicago sativa	2	0.7016
D-aminoacyl-tRNA deacylase	Q8IIS0	DTD_PLAF7	Plasmodium falciparum	2	0.7015
Queuine tRNA-ribosyltransferase	P28720	TGT_ZYMMO	Zymomonas mobilis subsp. mobilis	2	0.7013
Fibroblast growth factor receptor 2	P21802	FGFR2_HUMAN	Homo sapiens	2	0.7011
Protein kinase C iota type	Q62074	KPCI_MOUSE	Mus musculus	2	0.7010
HTH-type transcriptional repressor PurR	P0ACP7	PURR_ECOLI	Escherichia coli	2	0.7004

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